Degraded limonoids from Melia azedarach and biogenetic implications

被引:40
作者
D'Ambrosio, M [1 ]
Guerriero, A [1 ]
机构
[1] Univ Trent, Chim Bioorgan Lab, I-38050 Povo, Italy
关键词
Melia azedarach; Meliaceae; chinaberry; degraded limonoids; teracrylmelazolide A; teracrylmelazolide B; melazolide A; pyroangolensolide; 30-hydroxyfraxinellone; 9; alpha-; and; beta-hydroxyfraxinellone;
D O I
10.1016/S0031-9422(02)00107-3
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The roots of Melia azedarach yielded three new degraded limonoids: teracrylmelazolide A, melazolide A and teracrylmelazolide B, possessing a previously undescribed skeleton. The known pyroangolensolide, fraxinellone and its three derivatives, 30-hydroxyfraxinellone, 9alpha- and 9beta-hydroxyfraxinellone, were also isolated. Their stereochemisty was elucidated on the basis of spectral data and chemical reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:419 / 424
页数:6
相关论文
共 9 条
[1]  
AKHYLA A, 1999, FORTSCHR CHEM ORGAN, V78, P47
[2]  
[Anonymous], STEREOCHEMISTRY FUND
[3]   A DEGRADED LIMONOID FROM FAGAROPSIS-GLABRA [J].
BOUSTIE, J ;
MOULIS, C ;
GLEYE, J ;
FOURASTE, I ;
SERVIN, P ;
BON, M .
PHYTOCHEMISTRY, 1990, 29 (05) :1699-1701
[4]  
DREYER DL, 1968, FORT CHEM ORG NAT, V26, P190
[5]   SYNTHESIS OF DL-PYROANGOLENSOLIDE [J].
FERNANDEZMATEOS, A ;
BENITO, MG ;
COCA, GP ;
GONZALEZ, RR ;
HERNANDEZ, CT .
TETRAHEDRON, 1995, 51 (27) :7521-7526
[6]   A CHIROPTICAL METHOD FOR DETERMINING THE ABSOLUTE-CONFIGURATION OF ALLYLIC ALCOHOLS [J].
HARADA, N ;
IWABUCHI, J ;
YOKOTA, Y ;
UDA, H ;
NAKANISHI, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5590-5591
[7]   Degraded limonoids from Melia azedarach [J].
Nakatani, M ;
Huang, RC ;
Okamura, H ;
Iwagawa, T ;
Tadera, K .
PHYTOCHEMISTRY, 1998, 49 (06) :1773-1776
[8]   HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].
OHTANI, I ;
KUSUMI, T ;
KASHMAN, Y ;
KAKISAWA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096
[9]   Synthesis and biological activities of degraded limonoids, (+/-)-fraxinellonone and its related compounds [J].
Okamura, H ;
Yamauchi, K ;
Miyawaki, K ;
Iwagawa, T ;
Nakatani, M .
TETRAHEDRON LETTERS, 1997, 38 (02) :263-266